I would like the 2nd gen if it includes force touch and a better charging solution for the pencil. Also I would like to know if its better than Surface pro 4 in terms of drawing with the pencil/stylus. I think iPad Pro is a great canvas, of course iOS doesn't have all the features of Windows 10 which is a touch/tablet friendly, desktop OS, but not touch/tablet designed OS. From my point of view it all comes down to well designed apps, apps designed and coded for a mobile device, apps designed and coded for desktop with sharing capabilities to allow customers moving from one to another anytime during their workflows. These are the apps I would mostly use if I had one: Mail, Safari, Storyist, SketchBook, Graphic, Pages, Keynote, Notes, Remote Desktop, Udemy, Manga Meow, iCircuit and Chromecast. And I would keep a smaller iPad as well because is the tablet that can replace your magazine... in the restroom.
Excuse my language, English is not my mother tongue.